The conversation revolves around Jay Williams' transition from being a superstar college athlete to being a media personality and entrepreneur. After a severe accident that ended his NBA career, Jay reinvented himself through his involvement with ESPN and by developing a keen interest in business and investment, paving a new path for athletes who transition into fields like business and media.

The discussion explores the changing landscape of sports, media, and financial opportunities for athletes. Jay highlights the growing acceptance and intersection of sports and business, noting how athletes are now more openly engaging in entrepreneurship and media ventures alongside their sports careers. He shares insights into how this evolution is influencing perceptions and creating a new norm where athletes can discuss and invest in business ventures publicly.

Main takeaways from the video:

Please remember to turn on the CC button to view the subtitles.

Key Vocabularies and Common Phrases:

1. multi-hyphenate [ˈmʌlti-ˈhaɪfənˌeɪt] - (noun) - A person with multiple skills or occupations, often in diverse fields. - Synonyms: (polymath, generalist, versatile)

So, Alex, Jay is a multi hyphenate in a lot of ways.

2. inquisitive [ɪnˈkwɪzɪtɪv] - (adjective) - Showing a keen interest in learning or asking questions. - Synonyms: (curious, inquiring, probing)

He has an incredible appetite, very inquisitive, and is building a big business.

3. connotation [ˌkɒnəˈteɪʃən] - (noun) - An idea or feeling that a word invokes beyond its literal meaning. - Synonyms: (implication, suggestion, nuance)

Always, like, why such a negative connotation word?

4. bandwidth [ˈbændˌwɪdθ] - (noun) - The capacity for data transfer in a system or the range of ideas or concepts someone can manage. - Synonyms: (capacity, range, scope)

The bandwidth has extended.

5. transactional [ˌtrænˈzækʃənl] - (adjective) - Relating to or involving exchange or deals, especially in business. - Synonyms: (corporate, commercial, exchange-based)

They become very transactional, and they want it now.

6. vulnerability [ˌvʌlnərəˈbɪlɪti] - (noun) - The quality of being open to emotional hurt, criticism, or attack. - Synonyms: (fragility, susceptibility, openness)

There's a vulnerability that you showed and that he showed.

7. proclivity [prəˈklɪvɪti] - (noun) - A natural inclination or tendency to act in a particular way. - Synonyms: (propensity, inclination, predisposition)

Whenever people. I hear them talk about nil, the natural proclivity is to say.

8. entrepreneur [ˌɒntrəprəˈnɜr] - (noun) - A person who sets up and runs new businesses. - Synonyms: (businessperson, founder, capitalist)

We also know him really as one of the leading athletes turned entrepreneurs.

9. rev share [rɛv ʃɛr] - (noun) - Revenue sharing; the distribution of profits and losses among stakeholders. - Synonyms: (profit sharing, revenue allocation, dividend)

Whenever you talk about rev share Arod, then you start talking about, okay, how about workers comp?

10. sustainability [səˌsteɪnəˈbɪlɪti] - (noun) - The ability to maintain something at a certain level or rate over time. - Synonyms: (endurance, viability, permanence)

It allows you to build longer sustainability with the actual client.

How Jay Williams Reinvented His Brand After Basketball - The Deal

So, Alex, Jay is a multi hyphenate in a lot of ways. This is a guy who was a superstar college athlete, has a massive accident that sort of takes him out of the NBA and completely reinvents himself to the point where we know him from ESPN. We also know him really as one of the leading athletes turned entrepreneurs. He's a very good guy. And you know what? He has an incredible appetite, very inquisitive, and is building a big business. And I think he's a fascinating guy. And I think you'll find his interview very, very good and very intimate and very revealing. There's a vulnerability that you showed and that he showed that was pretty amazing to witness. So without further ado, Jay Williams.

All right, we like to start every show. Jay, oh, my gosh. I just introduced you myself. You introduce yourself and tell us who you are. How do I do that? However, you take all, take your time. Jay Williams, on air personality, own a media company. I invest. I followed him for a very long time, kind of geeking out to be here with you guys and just excited for the opportunity to chat. And where'd you go to college? Duke University for the Chicago Bulls. And we have a great common friend, obviously much closer to you than to me, but I'm a big admirer of Coach K.

Coach K, which we'll talk about later. Yeah, we're definitely, we're going to get into all of this. I feel like, for doing tv, I should have done a better job of introducing me. You want to take two? Yeah, no, that's good. That's good. People like it a little rough. I do want to ask you, I mean, we're going to talk about a ton of different things, but one of the reasons I know Alex and I were so fascinated to talk to you is given everything you just said about what you're doing, what you have done, it does feel to me like something new and different is happening in sports and media and culture right now.

Do you agree, and why do you think it is? So I'll give you guys some context to how kind of guys like Alex, I think, have really helped me expand my mind and how I think about this. I started a holding company when I first got into tv. Just called Clandestine Ventures. Right? And my mom, who just passed away a year ago, got rest or so. Always, like, why such a negative connotation word?

And I was always, because at ESPN, I couldn't let ESPN know about investing. I couldn't let ESPNA, you know, invested in a procurement company for sponsorships. Because it always got used against me. Like, I wasn't, you know, wasn't focused on my craft. And I just think now we have people that are unapologetically themselves, and this conversion between sports, finance, media. You know, you could talk about your portfolio on air. You can talk about my relationship with Adam Silver and obviously our Duke connection, and how it gives me different insight into team ownership and the CBA. I think now it's way more appreciated because there's a. The bandwidth has extended. Right. And now it's just not about polarizing conversation or about the game itself. It's about how you providing color to the commentary.

Do you feel that way, too? Cause I feel like. I mean, as Jay said, you were on the front end of this in terms of, you know, you tell the story about, you know, going into owners offices in your cleats and seeking advice, but, like, that wasn't the norm. And so does it feel different to you as well? No, I agree with Jay. To me, it was like a taboo to do anything else besides your core business.

And it's a little bit. You have to do it in the shadows. I started my real estate portfolio in my early twenties, but it was like a dark secret. And it's funny. The most grief I ever got in my entire career, far more than the PD suspension and all of that, which we'll get into later, is my contract. 252 in the year 2001. And the contrast between that announcement and Ohtani. Ohtani was a hero. He was celebrated.

I was villain 101. Darth Vader. So it's interesting how far things have gone. A lot of it, I think, is social media. Now. The power's gone to the athletes. Cause now they have a platform where they can fight back and back. You know, 25 years ago, you know, owners ran everything. You know, I was. I was. I was gonna ask you because I feel like there's this missing gap, Alex, has happened. Right. And you've been able to close that gap, but I see a lot of other athletes that are trying to focus on that and celebrities from going to becoming.

You're an asset, but how do you become the principal? How do you navigate doing tv while also now being a position to be an owner? Right. Which is how people. They may take that as commentary. How do you kind of play neutral in that regard? That's a great question. I mean, it helps that I commented on baseball and owning basketball. That's a big help. I think, for me, it's really thinking about it long term.

I think the biggest mistake I see young players is they become very transactional, and they want it now because that's how it is in basketball, right? You go to Duke for one or two years, and boom, you got a huge contract in business. I thought about it. How do I build a business over the next 50 or 60 years? So it's allowed me to discipline what I call the ten touch role. So I won't ask you to be my partner or jason until we have at least ten touches.

Now, touches can be a nice change of emails. It could be coffee, it could be this, it could be going to a game together. But after ten touches, that's enough time where we've built a relationship, and now we can maybe start thinking about doing something together, and it keeps you away from the one and done. Like, hey, I met you. Can you invest into my business? It kind of gives you time to breathe, so it's more transformative than transactional.

For sure. For sure. Cause I find there's a lot of that in my industry. Like, even in looking at some of the deals that other athletes have taken, I'm like, okay, well, what's your long term plan? It seems more like instinct. Cash grabs instead of actually having a brand strategy. And so how did you start to think about being a business person? And when is that something that, like, you're talking to coach K about? Are you talking to your parents?

Like, how does that start? So I got lucky. My dad worked at American Express for over 20 years, and my mom was a guidance counselor, so I used to watch her go back to school and receive multiple master degrees while I was in school. So you can imagine being in daycare, playing different sports, and my mom's, you know, going off to night school. But my dad would bring me into the city because I'm from New Jersey all the time. So I would take the train with him, and I would see him do his Windsor knot over and over again.

Because you prepare for the job you want, not for the job you have, right? Knowlt was the first black CEO that I've ever seen as a little boy. So, like, I'm, you know, even watching, like, Kamala Harris now run for president. Like, my two daughters see somebody that looks like them running for president, like, that's a monumental thing for what that could do for your psyche. So just knowing that my dad worked for a black CEO, I kind of became enamored with Ken Snow, Amex.

Then when I came to Duke, which is great, coach had me think that way. We started sending letters to Fortune 500 executives that had graduated from Duke, and we started inviting them down to North Carolina. Similar to how you did it with the Yankees. Right? I mean, there's a lot of commonality here because Duke was always called, like, the Yankees of college basketball, right? So with. And all that entails.

So all these guys would come down, and we just kind of picked their brain around what businesses they were in, how they scaled those businesses, how I should be looking at utilizing, like, my name, image, and likeness, what businesses should I be thinking about investing in, and how I should handle my approach to the NBA. It was life altering. So, with that in mind, I love the comparison between Duke and Yankees, because everyone that watches us, you have an opinion. It's not like you're indifferent.

You either love us or hate us, which is kind of cool. But my question to you is, at what point did you start crystallizing what a holding company would look like? What was your education behind it? So probably going into my sophomore year, I kind of. We lost in the sweet 16 to Florida, and I kind of got punked on the court. And it was one of those moments for me where I had a choice. I could have gone back home, spent some time with my friends back in New Jersey, but I'm kind of a competitive prick, Alex, in a lot of different ways in life.

And instead of going back home, I was like, you know, I just want to stay here. So I went to summer school. I started overloading in all my summer courses, and I just worked out every day, got a chance to play USA basketball, made the team, and I had this one game against Jason Kidd and Gary Payton where I not only held my own, but I did really well. And all these conversations just started with, oh, okay, like, Jay, you could be a first round draft pick.

Like, I went from not being on a draft board to all of a sudden that summer, being a first round draft pick, and then I just started averaging 23, 24 points a game. And people were saying, you could be the top pick in the draft. So I think during that time, we had never really prepped for all that stuff around finance. We thought this was. I was going to be a four year guy, just started receiving calls from, like, agents, financial advisors, accounting services, and then my father, my mother, and I, which is always tricky.

I was gonna ask you how you started dealing with that. Like, when your parents are kinda at the forefront of those conversations, and it's like, all right, well, we're gonna start, like, what's the limited liability corporation? What does this actually mean? What do we wanna name the LLC? Who are the members of the LLC? Are we gonna have an agent that's gonna be handling your accounting services as well? We just started having those real conversations, and frankly, that onboarding process while I was in my season, it felt overwhelming.

But I think the more I did it, it became part of my routine, you know, and I didn't feel as disturbed thinking about, okay, this is my business. Basketball is my business, but this is also my business. I shouldn't let that take away because, you know, I don't know if you dealt with this, that people say, well, the more you focus on that, it takes away from your focus on the field. That used to always happen to me. Yeah, yeah. For sure.

For sure. And I saw it just, like, as a compliment to my work. Right. And I made it to a point where I said, you know, for every hundred thousand dollars that I make or every 200, I can buy a million dollars worth of real estate, because you got 800 of debt, 200 of equity. So you kind of make it simple, right. And you kind of build it one block at a time. And then any role models that you had, who are some of those people that you've looked up to say, you know what? I like what they're doing. I can take a piece from him, piece from her. And now I have what I have. For me, that person is magic Johnson. That was a big mentor to me.

Started, sat down with me almost 30 years ago and kind of created the foundation of my company today. Do we share magic as somebody that you look as well? Because he's obviously the goat. I wore 32 all the time in high school. I couldn't wear it in college because Christian Layton had it. So literally, I took 22, which is just ten digits off, and I got that. But definitely magic for what he's been able to do real estate wise. Real estate is actually still a part of my portfolio I haven't really tapped into yet. Michael's entry point, Jordan just. I grew close to David falk.

I didn't go with David Falk. I went with Bill Duffy. David Falk, very well known agent. Yeah. Michael Jordan helped him, obviously, with the Jordan brand, everything. So just watching the way Michael. But also kind of hearing that story, I think for me, there was always this challenge because my father was so involved in business and my mother was participating in my business.

See, like, you know, can I be vulnerable with you guys, please? Of course. So you start finding about all these things that got. And it's weird. It would have probably crystallized different for me if I had played 15 years in the league. But when I got drafted, you want to give back to your family, right? So when you start learning that, hey, you're going to get gift taxed, anything you give over a certain threshold, like, okay, just let me put my parent, my family on the payroll.

All right. So my dad was a CFO, my mom was a CMO. You give people random titles, not that they're actually responsible for those titles, but we're trying to figure it out. I think when you start going through that process where you're paying your family. I had a lot of conversations with magic early around how do I take more ownership and knowing that this is my business, how do I delegate some of those responsibilities to my mom and my dad, which, when I got drafted, that changed for me.

They were my business partners while also being my mom and dad, which was a really weird. That's a lot of red tape involved in that, right? Cause you have a lot of people that are coming to you from different angles. And I don't know how to properly vet deals. I don't know how to properly vet people. I never had a lot of practical experience in that.

So I think leaning upon Grant Hill was another one because he played at Duke, what he's been able to do with his businesses. A part owner of the Atlanta Hawks, I tried to lean on those guys, but also my career was cut short. So, you know, my life took a different turn very abruptly after one year. So I didn't get a chance to really lean into those relationships as much as I wish I would have at the earlier stage.

I did that later. Yeah. Jason, I don't know about you, it's interesting. We have a great threesome here of people where you have african american, white and dominican. Right? I grew up with a single mom. Dad left at ten, and this changed my life. Jay. She had two jobs, secretary in the morning, she served tables at night. And we go into Publix one day and it's like a $75 bill, and she pulls out $55, and then we're short about 20 plus bucks or whatever, and she goes into this other little zipper, and she grabbed like 25, but it's not green, it's like red.

And I was like, mom, what's the funny money? And it was government money, food stamps. And I said, oh, my God, I have to, like, be the alpha. I have to be the leader of my family. But going back to your mom and dad, I can give my mother a dominican mom, any title. She's still going to be my boss. That's a little bit of take those three letters and you know where you can stick them. That's the thing about inheriting money, right?

It's now we see a lot of my other friends, a lot of the financial conversations that they had with their parents, you know, who were more successful. Their competency was way higher than me. So now I was being thrusted into this lifestyle where I was with the rich and the famous, but I didn't really learn about the underground underlying business of how to actually sustain that. So we were, everybody was being onboarded to wealth in a crash course.

And I think as my parents and my career started to build, a lot of that stuff, they often say when you make money, it reveals more of the challenges and difficulties. More money, more problems, and a lot of those family dynamics kind of started to play into the business as well. So that raises a really interesting thing about some of the work you're doing right now. Name, image, and likeness has changed everything in the college sports world. You see it right down the street from you.

At University of Miami. I feel like, writ large, you're doing a lot of work around this. Got a new show coming out. You're working with the University of Alabama quarterback. Now, all these conversations that you're talking about, that really only happened in a fairly limited way for a small number of people. They're happening across all of these sports, across college football, even at the high school level. So what's the advice that you give?

Having known what you know, but also seeing what you're seeing now around nil, I think first goes to the point that we were just making mention of, right when you start, like, let's say, crazy competitive, I want to work out for 8 hours a day, and I sleep for 8 hours. There's still 8 hours left in your day. Like, how do you start building your competency in finance right at an earlier age? Like, you should know what an LLC is and all for these kids now they're having a chance to make money.

Like, Jalen Moreau is making over a million dollars a year in nil now, as a 1920 year old young person. That's a lot for you and your family to handle. While you're handling a new coach coming in, replacing Nick Saban. While you're now learning how to work with the collective, which essentially is acting like the front office for the school and negotiating rates, how do you keep the main thing, the main thing, when the main thing is actually the money and the revenue that's being driven off of all this conference realignment, tv, media deal rights, and it's all the wild west for me.

I often start the conversation with, let's create a flatline. Let's understand what your business is like. Your main thing is the main thing, but this is also part of your main thing, right? So let's give the main thing in this totality, the time and the attention it takes, because if you want to be a billionaire, right, if you want to go from asset to principal, you need to put in the work. And by the way, reading two to 3 hours a day is putting in the work. Asking questions is putting in the work, having curiosity.

So I think that's the start. Number one, you also have to own your ip. So I think that's really big right now for him. So him and his teammate Tarrion Arnold, last year, they started this whole thing around link, let a naysayer know, which I thought was really smart, right? And it turned into the school's rallying cry. So they filed for trademark, the name, and I've never seen this happen before, where players have filed for trademark for a name that the school then kind of backed because Nick Saban was talking about.

Let all naysayers know. And had this virality moment last year where Pat McAfee on game day, where it just went everywhere. So they did a merchandising deal with the school. Right? So that sets precedent. So now, you know, they're sharing it at Rev with the school. And now we kind of create a digital diary series around that because I want him to be able to talk firsthand person around.

How do you navigate owning a name like that, dealing with the school, but also trying to win a national title, competing for the CFP, having the greatest coach of all time that is no longer there. Right. Not that you can control anything, Jay, but, like, how do you think about, like, what is your narrative and how you're seeing this and how you stay in alignment with what the school is doing? But how do we make the world see who you are a little bit as well, from a leadership perspective.

And we own that. And we're working with the brand now, Beast, which is actually gonna be a sponsor of the show, so we're able to tie his endorsement deal into the content, which is smart. And I just like that medium. And it's a proof of concept for us to see. How do you work with the collective? How do you work with, and also, at the same time, how do you build his own individual brand? And, like, how do you personally engage him?

I mean, are you talking to him most days. Like, what's the. How do you build that rapport where you become a trusted advisor to him? I think I'd be curious to see how you talk to Anthony Edwards. Right. Cause I've known ant for a while, too. I think it's more of a big brother approach here, as it like, okay, hey, look, if we're gonna do content, I don't think that answer puts you in the best position with the media.

Probably wouldn't say it like that. Maybe. How about this? Or when he gets frustrated about something. I don't understand why this deal works out. Okay, like, let me explain the nuances of this to you. To a degree. I think it's more of that relationship and helping him navigate. I'm not his agent. I'm not his financial advisor.

We're working with him on the media side. And working with him on your partner. Yes, I'm a partner with him. So, Jay, if we zoom out and you said the wild, wild west, I think that's exactly what it is. The nil Genie's out of the bottle. They probably never come back in. But a few questions. How do you feel about that kind of pros and cons, and is this something that is ultimately better for college sports? I do think it's better for college sports.

I still get frustrated at it, because whenever people. I hear them talk about nil, the natural proclivity is to say, well, okay, now athletes are going to pay. Well, actually, can we talk about rev share? That's different. So now we're starting to engage in that conversation. And whenever you talk about rev share Arod, then you start talking about, okay, how about workers comp? Just to be clear, what you're differentiating between is nil, where it's like they're getting paid by a brand or a collective or a company, versus rev share, where they are actually a real partner and employee, ultimately, of the school or the team.

Do I have that right? You already see Dartmouth basketball trying to do that. Right. And also, you know, like, so USC, UCLA, they go to the big ten. Now, you tell me how that fits the geographical footprint. It fits the financial footprint of the Big Ten. Right. Which I understand, but it's no longer about academics. Like, that travel schedule alone, from going from Socal to Columbus, Ohio, and then back. Like, you're gonna miss multiple days and then back to Maryland and then back to New Jersey and. Yeah, so I understand that.

But with that comes a lot of responsibility. So, you know, when you start having these types of conversations, then I go, okay, well, the university has representation, the leagues have representation. The players are allowed to have representation when it comes to branding and endorsement deals. But who is sitting at the table for the players? You need a union. If you're gonna become unionized, that means you're going to be an employee. So you have different employee rights, benefits.

And I think that's the next step in the natural evolution. Especially when we look at basketball and football, they generate the most revenue. And, you know, look at what happened to the Pac twelve. There's no longer the Pac twelve, right. It's disintegrated right in front of your eyes. Improbable. We didn't talk a lot about it, but that has been a really interesting, I feel like, new version of what media can be and is going to be.

What's your vision for that? I think it's one that's constantly morphing. I think I. It's like anything. I think when you go into it, you think it's going to be one way, and then you have to pivot a thousand times and it starts to take on a new shape and form. I think originally, at first it was okay as we look at. But Giannis, who I think is one of the biggest athletes in the world, touches three continents between Africa, United States and Europe.

How do we capture the value in the production and creative aspects along a lot of his endorsements? Cause you're seeing a lot of those are just outsourced to third parties. And I think once you kind of become integrated in the storytelling aspect of it, it allows you to build longer sustainability with the actual client. It's not a cash grab. Like, I think a lot of players look at endorsements as, okay, like, I have a five year deal worth $20 million.

That's great. And then when you get into, you know, four years and eight months, it's like, well, how do we start renegotiating that deal? So, for me, I'm like, no. Like, we're gonna sit at the creative table, right? We're gonna keep all the metrics and the data. We're gonna show you how we're adding value to your brand. And then I wanna get. I wanna pierce the conversation.

Cause I really think it bleeds into the portfolio from an investment opportunity. Once again, it goes through deploying capital. Then could we deploy capital and co invest alongside that athlete? Take a stake in what that entity is, principal principle, and then help scale it as well? I mean, similar to how Ryan Reynolds has built maximum effort. You've seen them do that with aviation gin. You've seen them do it with mint mobile.

You're seeing them do that with Wrexham. So I think having the pipes to amplify, to brand, but then also having the capital to deploy, having a seat at the table with the right board of athletes. And then I think, inevitably getting athletes to buy into this thing of shared economics. Yeah, like, I'm watching Steph do it and he's doing it successfully and very well in Lebron. Stephen Curry. Stephen Curry. Once again, first thing basis.

I'm sorry, Steph probably is another one. Yeah, Steph's another one. He's on the verge. He's on the verge. But, like, you know, how many things can you scale by yourself, right? So, you know, as an athlete, I think I'm built to say, hey, I can win a national championship without Mike Dunleavy or without Carlos Boozer or without a rod.

So then, you know, where is there a world, for lack of better terminology, like, you know, like a multifamily office in which five or six guys are coming together and they're saying, okay, how do we add value? Maybe we have a pool of capital here that's not ours, but we can deploy capital from. We can then co invest with that. But then how do we add value collectively with having the brand strategy and coming to the table with a vision that's just saying, hey, I'm at the table with capital.

I think, to me, that's where you receive compound interest over time and you're creating enterprise value. So I want to take, as we all say in our collective business, a hard pivot here and go back to something you mentioned earlier, which is, I dare say, the pivotal moment in your life when you're in a. A terrible accident right as you come into the league, and it changes the entire direction for you.

Tell us what that moment meant for your life, but also for your business career. Cause it changes what your job is going to be. I would love to know how it changed you as a burgeoning business person is how you defined yourself. Yeah, well, first off, I think it gave me a, no pun intended, like a real crash course in how hard and cold business could be. I've been a part of a lot of deals since.

Sometimes when you have money in a deal, you're forced to look at things way more objectively because your money is the asset in the deal. When you're the asset yourself, it's hard not to become emotionally tied to that. So I remember watching the Bulls draft Kirk Heinrich, who I just played the year prior at Kansas and did work against him to replace me, essentially in my hospital bed. So having conversations with Jerry Reinsdorf, understanding and hearing firsthand what their business strategy was, was a hard pill for me to swallow.

And it's crazy. Like, thinking about it was one hell of a business strategy. I mean, it's the right plan, right? It's the right plan that all of us would do. But when you're hearing that as the asset on the other end in the hospital bed, that led me into a deep state of depression. I mean, I had two attempts at suicide that I've talked openly about, but I think that forced me all of a sudden to start over again after I went through a couple of years of depression.

I really want to understand basketball and the CBA and how it worked. And actually it led me down the path with risk mitigation as well, because when you start receiving all these bills, you're like, well, hold on a second. How am I going to pay for these 13 plus surgeries? So the bulls kept me on their insurance. I had some challenges later with disability that I had to work through, but it opened my eyes to risk mitigation in a completely different aspect, which kind of led me down the path when I made my first really big investment in an insurance brokerage firm, because I started to understand about wholesale, I want to kind of sit in between the middle.

It really opened my eyes up to the under the table businesses associated with basketball, more importantly. And I really started studying the CBA under a guy named Charlie Grantham. I tried to become an agent. I thought that was like my first step into the world because I wasn't going to play anymore. And then it just, things became difficult because you realize when you're actually working for an agency, you spread a lot of money out to 501s, which are essentially AAU programs, and that was still deemed illegal at that time.

And a news reporter broke the story on Yahoo. Sports that even though I wasn't the main agent but associated with the agency, that we had paid Kevin Love's AAU team. And it was just one of those things where it was like, okay, how am I, how am I going to do this? You know, ive lost the ability to connect with players because if it becomes public, thats my mantra to a degree, and how do I kind of change that narrative about me?

So I got involved in tv, and thats when I really, I was like, okay, now I see how media works. I see how this one article came out, how it affected me. I frankly, started the process of writing my book. Then I was like, okay, I'm going to change this narrative. I'm no longer going to be the victim to my motorcycle accident. I'm going to start thinking about how I use my accident to build off of and kind of lean into what I want to become business wise.

And I think that was the first step. Like, in pr, it's like crisis management, and kind of starting that step in media, working for ESPN, making $35,000 a year, which is another humble kick to the gut. And I started understanding media, working in media, and I started the process of writing my book because this is something else we have in common.

And I was telling Jay, like, in 14, I served the year suspension for Pedus, and my whole world kind of fell apart. And, I mean, I think it's very public now that I've done over twelve years of therapy. I continue to be in. It is huge part of my life. But I had built this incredible career, and I was almost 40, and I'm just like, it was so scary to have to think about, oh, my God, am I gonna have to scratch everything and start all over again like that?

I was below, like, ground zero. Below ground zero for different reasons, obviously, than yours, but nevertheless, we had to build it back up from ground zero. I mean, you and I have talked about this a lot. I mean, one of the first in depth things that we did was essentially me asking Alex a question of, why did you even decide to reengage, you know, because there's a version of this, certainly, for you, where you're just like, all right, I'm good.

I'm going to go live on an island or do whatever. I'm going to remove myself from public. I'm not gonna play, or I'm not gonna certainly get out there. What was your thought process? I mean, like, Jay, very much depressed because you've worked so hard to this point, right? And you feel like you're now set up to win or reap the benefits of your great work in thousands and thousands of hours of commitment and dedication.

But ultimately, why I think Jay and I probably didn't go to an island is because we're both competitors. And I like that competitoring prick. I'm gonna steal that. Cause, I mean, I'm a nasty competitor, almost too competitive. And I felt like I had something else. I had another chapter in me, and I was too young to just give up. I mean, it's not in our DNA to give up. I don't know if I had suicidal but whatever the stop before that is, that was probably there because it's such a scary thing to be in a place where you've built it, and now you're at ground zero.

Literally ground zero, below ground zero. Like, I felt like if I got up to the lobby, that was a win. And I also felt like there was millions of kids out there that don't have parents that are great mentors or single parents like my mother, who don't have that. And I felt like I had a lot to offer for those kids to at least learn from my mistakes. And that was really the thesis of wanting to come back is to make an impact.

It was too far away from, you know, I want to go back and play baseball, or I want to go back and go to the hall of fame, or I want to go back and build an empire. It was really about, like, I know I have another chapter. I don't know what that looks like, but I'm going to give it a go. How'd you learn how to tell yourself a different story?

Cause I know that was, you know, playing at Duke's when we were playing the Yankees. Like, we're on tv all the time, right? So, like, before, when I would walk in rooms, whether that was business or personal, it would be like, that's Jay. He's, like, number two pick in the draft place for Chicago Bulls. He's on I 90. He's on the billboard. He is Michael Jordan's locker.

So all of a sudden, I look and, like, are you okay? Like, it was completely. It was a different entry point. I would even sit down at business meetings, and, like, some of these higher level executives would start the conversation for there, and I feel like I would have to drag myself out of the basement to get to the lobby level. Like, how'd you. How'd you deal with that from a start perspective? I just started leading with the worst.

I started leading with that. Beat them to it. Beat them to it. Beat them to the spot. Right? And it's kind of what you started to do with your book or your story. And I felt like if you start with the worst, then we can get better from there. And if you want to throw me out of the meeting, let's just do it in the first ten minutes. That way I don't waste your time, you don't waste my time, but I feel like when you own things and then you talk about the lessons learned, at least you set the foundation to show that you have self awareness.

And I see this from a lot of young kids. That, or just people in general, that they make mistakes, but their self awareness still hasn't gotten to where it needs to be. And what I sense is that when you win a championship where you sign a big contractor, you're that number two pick from the bulls or the Yankees or whatever, self awareness decreases, and ego increases. And I wake up every morning with two prayers. I want to enhance my self awareness and decrease my ego, and I think that's my happy spot. Yeah, that's one way that I did it.

Yeah, I think I learned that throughout that process. I've always kind of been enamored with c level executives. I've always wanted to be one. Yeah, me too. And it's amazing how many people I talk to that have gone through challenges within their businesses where filing for bankruptcy or losing money for investors. I think I recognize while I was writing my book and having all these conversations, oh, like, everybody's had a motorcycle accident in some form or fashion.

Everybody's had some kind of crash. Like, ours may be more extreme than others or more public than others, but maybe that's a place to actually build a bridge between myself and people, to actually not come to the room with more of my ego, but to be more self aware and then to actually form more of a community. And so how do you start building from there? I mean, so, with all of that in mind, you're doing work on yourself, but you also have to do the work. You know, you have to figure out, like, who you're gonna be and what you're gonna do and candidly, what you're gonna contribute.

You know? I mean, we talk about this all the time in terms of, like, what your. What your mission is gonna be. So how do you hone that over time, and who do you go? I mean, is this something where you go to coach K? I know Alex has sort of almost like a board of advisors that he. Yeah, Coach K scratched three copies of my book and told me, bring this back when it's better.

So, yes, yes, Coach K is on the respective board. And so how do you go about building that? Well, I did form a personal board for some people that I had admired, that I reached out to in college, and I get beat up. Like, it's like a real. It's like a real board meeting. Like, you know, really. All right, Q one. Where are we? Like, what are we doing? Like, what's the portfolio look like?

And we go through that, but then we go into, like, me personally, what's the marriage look like? What the kids like, how we balancing it. Like, it's like, I really get pushed and tested, which I very much appreciate. But just to go back before, like, I really leaned into media, because instead of just trying to go off and invest in all these different things, I'm like, all right, what is my platform? Like, basketball was my platform before.

What is my platform? And I think learning media and studying it and then studying how to be effective at it, but also how to be different than what I saw on tv. One of the things I think you do well, which I think is a huge gap between, kind of the sports community, entertainment community, versus the business community. I love the way you reach out and you're not afraid.

Where did you get that from? And you should be doing a lot more of that because you on tv and you reaching out to be with great people, whoever you think those are, is the best way to grow your business. I think I just have an insatiable appetite, you know, like, and it's like, even when I reach out to you, I want to be an owner one day of a team. Right? Understanding what teams are coming on the marketplace, what's happening in Las Vegas for the NBA?

Is there a team in Mexico City? What's going to happen in Europe? The explosion of NWSL and their new media rights. The WNBA, which is interesting entry point from an investor perspective. Professional bull riding, PBR, that league, cell, GP, understanding where all these leagues are coming from and how to actually bet those opportunities. That's number one. Right?

I think you are on point. And that goes just to close the loop on this story. I think when I was learning tv, I think I saw that gap, and I did this show called the best shot, and it was with LeBron and Maverick, and it was when they were launching Spring Hill. Maverick Carter, LeBron James business partner. Yeah. Sorry. I should be a little bit more. That's all right. That's why I'm here.

Yes. And I saw them building this media empire, but then also I saw how they were utilizing the media empire for a lot of their investments. And I also saw, from my perspective, all of a sudden, on the show now, I'm an executive producer, and I'm talent. I'm like, oh, okay. I can eat on both ends. It was very fascinating. So then, understanding that dynamic and how they worked, then I started working with Rich Kleiman and Kevin Durant when we launched the boardroom.

Now, that was tricky, because I had to sell the boardroom to the company I was working for. Right. So that allowed me to have a lot of different conversations with Jimmy Portaro, Connor Schell, any ESPN's 30 for 30 with Rich and Kevin? But it was, once again, it just served proof of concept that I was with Serena here at Williams about her venture firm. Right. Serena is one that you could just say, serena, I don't know.

Some people, you know, you gotta be first name basis. But then I start sitting down with Steve Ballmer and Josh Kroenke and hearing about all the teams they own and start learning about tax abatements and how to think about that when you're actually building a stadium in Inglewood. Right. Some of the challenges that come along with that. And then I would listen to high level athletes who actually were pretty competent in business, but still didn't sound as competent or still were somewhat, a little bit afraid to sit at the actual table. Alex, do you still get that, like, with certain athletes, like who are. They want to be in the room and they could be in the room and they can listen, but they don't know how to take it to that next step as a business person.

Yeah. I think a lot of it is because they're never alone in a room. Yes. I would tell athletes, get yourself in the room and go alone. That's the greatest advice they can give you, because if not, inevitably, they're going to talk to your agent or your manager or whatever. Now, it's okay to bring one person or whatever, but get in the room, get uncomfortable and feel comfortable in the uncomfortable, especially sitting in that table.

And I love the fact that you have, quite honestly, the. We say the cojones, maybe moxie. Yeah, see, that's a Georgetown word. Georgetown. Duke, I feel very much imposter right now. Okay. I have, like, Dominican University here. But, Jay, with you, I love that you can verbalize. That's part of it. And to say it, first of all, it's hard to do it in your mind.

To say it in your mind. You're saying it publicly. I want to be an owner one day. That's awesome. But how does the J. Williams holding company look in five years if you had it your way? Hmm. I think having capital to deploy is very important to have a seat at the table. So I think what you might see is I always keep my foot within media from an ownership perspective because I understand that business and I understand where that business is going.

But I think the sports marketplace is really fascinating for me, Alex, being able to have capital behind an entity with a media marketing branding arm where I can look at certain investments and I can look at their operating teams and effectively take shots at those type of assets and scale that slowly. And I don't want to use the term private equity because that's just like, you know, everybody, I want to be involved in private equity, or every athlete wants to have a family office, but a team of brand strategists and a chief investment officer in which we could look at different assets and then marry ip to certain athletes that I think actually want to work and actually want to have a seat at the table, because I do see that correlation.

I am able to have conversations with certain individuals where I'm like, I'll bet on you, because I know that you would like to work. And I also. We have access to so much stuff, right? So it's like somebody's like, hey, Jay, you know, in five years, if this explosion continues to happen within the collegiate market, you know, what's one of your port codes? I would say I would love to own a significant piece of Duke basketball.

Right? Would love to own a significant piece of Ohio state football. I think that's going to be a marketplace that's being tinkered around right now. But then also thinking about all these traditional athletic companies, athletic departments are still very archaic. And now I think you're seeing the same way private equity is entering the NFL. Conversations around Aries and other PE firms entering that market, I think that's going to happen on the collegiate market. And how could you help Duke generate more revenue and be more profitable?

By having experts associated with Duke basketball from a branding perspective, from a content perspective, from a media rights perspective. So I think in five years, I think that's the direction I'm going. And I think similar to you, I think I always love commentary, but I want to be insightful with my commentary. And I also think similar to what we're doing with Jalen, I like telling things more from. From the player businessman perspective instead of just the player perspective.

I think I'm starting to learn that that could be my sweet spot. That doesn't allow me to ultimately hurt my relationships, but still be true to myself and what I see. Well, that's the. I mean, you talk about magic all the time, basically saying you can get in the room, you know, like, you guys can do the thing. That is certainly hard for a journalist, but, like, hard for an everyday day person just to get into the room because everybody wants to know exactly what you're talking about. What's it like? What's it like shooting that free throw? What's it like taking that three. What's it like being at that home play and then you're in, and then you prove yourself and the relationship begins, etcetera. I agree with that.

Jason and Jay, the thing is that I've studied so many of the titans, right? But what they are expecting is they're expecting for you to come in the room, be a nice guy, and take a picture and sign autographs, and then we say bye bye to you. Now we put you on your way. They're not expecting you to have a real team, and they're definitely not expecting you to follow up. And I think that's where most athletes, you know, 20% of the athletes asked for the meeting.

Probably 1% of those 20 follow up in a real way. And you got to follow up. Right. And you got to be long term thinking, because if most athletes come in with high expectations, one meeting, big deal. It doesn't really happen like that. Unless you're Tiger or maybe Tom Brady or something. That is just one and done and you're good. But it's just who's going to be persistent, to hang around, hang around, keep coming back, and stay focused on what you really need and want, you know?

All right, let's do our rapid fire now. I think you're going to be really good at this. I think you're going to be really good at it. All right, I'll start, and then you. Rules that. You keep it tight. Keep it tight. You just keep it tight. Do I get a chance to ask any back to you guys? No. We'll see how it goes. At the end of.

What's one word to describe your deal making style? Patient. What's more important to you, your instincts or data? I really value data, but I think it's coming down to instincts and gut. Who people are. Who is your dream deal making partner? I mean, it's David Rubenstein. I thought you were gonna say, Jason, what's the best piece of advice you've received on deal making or business? Never run. Always walk with pace. Same question.

What's the worst advice you've ever been given? Worst advice came from an athlete. This is bad. Actually, a successful athlete. Jay, the more deals, the better. Oh, wow. Actually, none. Oh, interestingly so. That's the best answer we've ever gotten tangible. What's your hype song? Before you go into a big meeting or negotiation.

This is weird. I've been listening to a lot more classical orchestras. I like to try to be calm, take the emotion out of the dance. Any specific composer you like? I'll go with the old school, like a little patty labelle. Okay. A fun fact about yourself that your colleagues will be surprised to hear about. Loyalty and transparency is very important to me. Cause I didn't have that a lot of my life. I had a lot of times where a lot of deals or a lot of people tried to pull the wool over my eyes. And I think I always try to operate from that space. Nice. Mmm. All right, well, this has been a huge treat for us. Thank you so much, Jay Williams. Thank you. Good stuff, guys. Thanks. Thanks a lot. Thanks, Jake. Thanks, Mandy.

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